(4R,4aR,7aR,12bS)-9-methoxy-2,4,4a,5,6,7a-hexahydro-1H-spiro-[4,12-methanobenzofuro[3,2-e]isochromene-7,2′-[1,3]dioxolane] | 1426537-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (4R,4aR,7aR,12bS)-9-methoxy-2,4,4a,5,6,7a-hexahydro-1H-spiro-[4,12-methanobenzofuro[3,2-e]isochromene-7,2′-[1,3]dioxolane]
• 英文别名: (1'S,5'R,13'R,17'R)-10'-methoxyspiro[1,3-dioxolane-2,14'-4,12-dioxapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene]
• CAS: 1426537-72-5
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: CBSNNFAKHOTAOB-GGBBIFEXSA-N

物化性质

• 沸点：
  491.5±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,4aR,7aR,12bS)-9-methoxy-2,4,4a,5,6,7a-hexahydro-1H-spiro-[4,12-methanobenzofuro[3,2-e]isochromene-7,2′-[1,3]dioxolane] 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以95%的产率得到(4R,4aR,7aR,12bS)-9-methoxy-1,2,4,4a,5,6-hexahydro-4,12-methanobenzofuro[3,2-e]isochromen-7(7aH)-one
  参考文献：
  名称：

  Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

  摘要：

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.

  DOI：

  10.1021/jo3026753
• 作为产物：
  描述：

  二氢可待因酮 在 sodium tetrahydroborate 、 三甲基氯硅烷 、 双氧水 、 mercury(II) trifluoroacetate 、 三氟乙酸酐 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 76.03h， 生成 (4R,4aR,7aR,12bS)-9-methoxy-2,4,4a,5,6,7a-hexahydro-1H-spiro-[4,12-methanobenzofuro[3,2-e]isochromene-7,2′-[1,3]dioxolane]
  参考文献：
  名称：

  Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

  摘要：

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.

  DOI：

  10.1021/jo3026753

文献信息

• Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity
  作者：Robert D. Giacometti、Jan Duchek、Lukas Werner、Afeef S. Husni、Christopher R. McCurdy、Stephen J. Cutler、D. Phillip Cox、Tomas Hudlicky

  DOI：10.1021/jo3026753

  日期：2013.4.5

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.